EP1480953B2 - Verfahren zur herstellung von aripiprazole - Google Patents

Verfahren zur herstellung von aripiprazole Download PDF

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Publication number
EP1480953B2
EP1480953B2 EP03780889A EP03780889A EP1480953B2 EP 1480953 B2 EP1480953 B2 EP 1480953B2 EP 03780889 A EP03780889 A EP 03780889A EP 03780889 A EP03780889 A EP 03780889A EP 1480953 B2 EP1480953 B2 EP 1480953B2
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EP
European Patent Office
Prior art keywords
carbonate
group
alkali metal
preparing aripiprazole
hydroxide
Prior art date
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Expired - Lifetime
Application number
EP03780889A
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English (en)
French (fr)
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EP1480953A1 (de
EP1480953B1 (de
Inventor
Hisayuki Tsujimori
Tatsuya Yamaguchi
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Otsuka Pharmaceutical Co Ltd
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Otsuka Pharmaceutical Co Ltd
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Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd
Priority to SI200330153T priority Critical patent/SI1480953T2/sl
Publication of EP1480953A1 publication Critical patent/EP1480953A1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • EP-A-367141 it is mentioned that the above-mentioned reaction can be carried out, if necessary, by adding an alkali metal iodide such as potassium iodide, sodium iodide or the like as the reaction accelerator; and in the working examples thereof ( EP-A2-367141 , page 5, lines 42-44) sodium iodide is used as the reaction accelerator. According to the process described in EP-A-367141 , however, yield of the objective aripiprazole cannot exceed about 80%, even if the reaction accelerator is used.
  • an alkali metal iodide such as potassium iodide, sodium iodide or the like
  • sodium iodide sodium iodide
  • WO 03/026659 is prior art in the sense of Art. 54(3) EPC. It relates to the manufacture of low hygroscopic aripiprazole.
  • raw aripiprazole is prepared as follows in a yield of 74.2%.
  • the process of the present invention is quite advantageous as an industrial production process of aripiprazole.
  • the crystals thus obtained were washed with 240 ml of water and dissolved in 900 ml of ethyl acetate, and an azeotropic mixture of water/ethyl acetate (about 300 ml) was distilled out under reflux. The remaining solution was cooled to 0 to 5°C, and the deposited crystals were collected by filtration. The crystals thus obtained were washed with 120 ml of ethyl acetate and dried under a reduced pressure of 50 Torr, at 50 to 60°C for 3 hours to obtain 98.4 g of aripiprazole (yield 92.8%, purity 99%). mp. 140°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Quinoline Compounds (AREA)

Claims (9)

  1. Verfahren zur Herstellung von Aripiprazol, dargestellt durch Formel (1):
    Figure imgb0007
     durch Umsetzen einer Carbostyrylverbindung, dargestellt durch Formel (2):
    Figure imgb0008
     worin X ein Halogenatom, eine Niederalkansulfonyloxygruppe, eine Arylsulfonyloxygruppe oder eine Aralkylsulfonyloxygruppe darstellt,
    mit einer Piperazinverbindung, dargestellt durch Formel (3):
    Figure imgb0009
     und/oder einem Salz davon in Wasser und in Gegenwart einer anorganischen basischen Verbindung in einer Menge von 0,5 bis 10 mol pro Mol der Carbostyrylverbindung (2),
    dadurch gekennzeichnet, dass die Piperazinverbindung der Formel (3) und/oder ein Salz davon in einer Menge von 1 bis 1,5 mol pro 1 mol der Carbostyrylverbindung der Formel (2) verwendet wird.
  2. Verfahren zur Herstellung von Aripiprazol gemäss Anspruch 1, wobei das Verfahren eine einzige Art einer anorganischen basischen Verbindung verwendet, und die anorganische basische Verbindung ein Alkalimetallhydroxid, ein Alkalimetallcarbonat oder ein Alkalimetall ist.
  3. Verfahren zur Herstellung von Aripiprazol gemäss Anspruch 1, wobei das Verfahren zwei oder mehr Arten von anorganischen basischen Verbindungen als Mischung verwendet, und die Mischung der anorganischen basischen Verbindungen eine Mischung eines Alkalimetallhydroxids und eines Alkalimetallcarbonats ist.
  4. Verfahren zur Herstellung von Aripiprazol gemäss Ansprüchen 2 oder 3, worin X ein Halogenatom ist.
  5. Verfahren zur Herstellung von Aripiprazol gemäss Anspruch 2, worin X ein Chloratom ist und die anorganische basische Verbindung ein Alkalimetallcarbonat ist.
  6. Verfahren zur Herstellung von Aripiprazol gemäss Anspruch 3, worin X ein Chloratom ist.
  7. Verfahren zur Herstellung von Aripiprazol gemäss Ansprüchen 2 oder 3, worin das Alkalimetallhydroxid Natriumhydroxid, Kaliumhydroxid, Cäsiumhydroxid oder Lithiumhydroxid ist.
  8. Verfahren zur Herstellung von Aripiprazol gemäss Ansprüchen 2, 3 oder 5, worin das Alkalimetallcarbonat Natriumcarbonat, Kaliumcarbonat, Cäsiumcarbonat, Lithiumcarbonat, Lithiumhydrogencarbonat, Natriumhydrogencarbonat oder Kaliumhydrogencarbonat ist.
  9. Verfahren zur Herstellung von Aripiprazol gemäss Anspruch 2, worin das Alkalimetall Natrium oder Kalium ist.
EP03780889A 2003-01-09 2003-12-18 Verfahren zur herstellung von aripiprazole Expired - Lifetime EP1480953B2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SI200330153T SI1480953T2 (sl) 2003-01-09 2003-12-18 Postopek za pripravo aripiprazola

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2003002996 2003-01-09
JP2003002996 2003-01-09
PCT/JP2003/016256 WO2004063162A1 (en) 2003-01-09 2003-12-18 Process for preparing aripiprazole

Publications (3)

Publication Number Publication Date
EP1480953A1 EP1480953A1 (de) 2004-12-01
EP1480953B1 EP1480953B1 (de) 2005-11-02
EP1480953B2 true EP1480953B2 (de) 2010-08-18

Family

ID=32652780

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03780889A Expired - Lifetime EP1480953B2 (de) 2003-01-09 2003-12-18 Verfahren zur herstellung von aripiprazole

Country Status (19)

Country Link
US (1) US6995264B2 (de)
EP (1) EP1480953B2 (de)
JP (2) JP5797090B2 (de)
KR (1) KR100583667B1 (de)
CN (1) CN1263742C (de)
AR (1) AR042702A1 (de)
AT (1) ATE308524T1 (de)
AU (1) AU2003288755C1 (de)
BR (2) BR0305500A (de)
CA (1) CA2676216A1 (de)
DE (1) DE60302139T3 (de)
DK (1) DK1480953T4 (de)
EG (1) EG23557A (de)
ES (1) ES2250919T5 (de)
MX (1) MXPA04002519A (de)
MY (1) MY129831A (de)
SI (1) SI1480953T2 (de)
TW (1) TWI258470B (de)
WO (1) WO2004063162A1 (de)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7714129B2 (en) * 2003-12-16 2010-05-11 Teva Pharmaceutical Industries Ltd. Methods of preparing anhydrous aripiprazole form II
US7504504B2 (en) * 2003-12-16 2009-03-17 Teva Pharmaceutical Industries Ltd. Methods of preparing aripiprazole crystalline forms
DE202005020539U1 (de) * 2004-02-05 2006-09-28 Teva Pharmaceutical Industries Ltd. Aripiprazol
US7507823B2 (en) 2004-05-06 2009-03-24 Bristol-Myers Squibb Company Process of making aripiprazole particles
KR101041551B1 (ko) * 2004-10-08 2011-06-15 수벤 라이프 사이언시스 리미티드 아리피프라졸 제조를 위해 유용한 신규 중간체와 신규중간체 및 아리피프라졸 제조 방법
US20060079689A1 (en) * 2004-10-12 2006-04-13 Vladimir Naddaka Processes for preparing and purifying carbostyril compounds such as aripiprazole and 7-(4-halobutoxy)-3,4-dihydro-2(1H)-quinolinones
WO2006053781A1 (en) * 2004-11-18 2006-05-26 Synthon B.V. Process of making crystalline aripiprazole
CN1303068C (zh) * 2005-01-11 2007-03-07 中国人民解放军第二军医大学 一种阿立哌唑的制备方法
TWI320783B (en) 2005-04-14 2010-02-21 Otsuka Pharma Co Ltd Heterocyclic compound
EP1933814A2 (de) 2005-09-15 2008-06-25 Elan Pharma International Limited Nanoteilchenförmige aripiprazol-formulierungen
JP2008537540A (ja) * 2005-12-22 2008-09-18 テバ ファーマシューティカル インダストリーズ リミティド アリピプラゾールの粒径を小さくする方法
US20070149782A1 (en) * 2005-12-23 2007-06-28 Michael Brand Methods of preparing a crystalline form of 7-(4-chlorobutoxy)-3,4-dihydro-2(1h)-quinolinone and the use thereof in the synthesis of Aripiprazole
DE602007001620D1 (de) * 2006-04-10 2009-09-03 Ranbaxy Lab Ltd Verbesserter Herstellungsprozess für Aripipirazol
RU2497819C2 (ru) 2007-05-21 2013-11-10 Ривайва Фармасьютикалс, Инк. Композиции, синтез и способы применения атипичных нейролептиков на основе хинолина
US8207163B2 (en) 2008-05-27 2012-06-26 Reviva Pharmaceuticals, Inc. Compositions, synthesis, and methods of using piperazine based antipsychotic agents
CN101781246B (zh) * 2009-01-15 2012-02-29 成都康弘药业集团股份有限公司 一种合成阿立哌唑的改进方法
EP2400968B1 (de) 2009-02-26 2016-09-28 Reviva Pharmaceuticals, Inc. Zusammensetzungen, ihre synthese und verfahren zur verwendung von arylpiperazinderivaten
JOP20200109A1 (ar) 2012-04-23 2017-06-16 Otsuka Pharma Co Ltd مستحضر قابل للحقن
EP3294724A4 (de) * 2015-05-08 2018-11-21 Davuluri, Ramamohan Rao Verbessertes verfahren zur herstellung von aripiprazol mit verringerter partikelgrösse

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3034237A1 (de) † 1979-09-18 1981-04-16 Otsuka Pharmaceutical Co. Ltd., Tokyo Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel
WO2002090351A1 (en) † 1999-11-24 2002-11-14 Otsuka Pharmaceutical Co., Ltd. Process for producing carbostyril derivative
EP1330249A1 (de) † 2001-09-25 2003-07-30 Otsuka Pharmaceutical Co., Ltd. Aripiprazole wirkstoff mit niedriger hygroskopie und verfahren zu ihrer herstellung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54130587A (en) * 1978-03-30 1979-10-09 Otsuka Pharmaceut Co Ltd Carbostyryl derivative
JP2608788B2 (ja) * 1988-10-31 1997-05-14 大塚製薬 株式会社 精神分裂病治療剤
US5006528A (en) * 1988-10-31 1991-04-09 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3034237A1 (de) † 1979-09-18 1981-04-16 Otsuka Pharmaceutical Co. Ltd., Tokyo Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel
WO2002090351A1 (en) † 1999-11-24 2002-11-14 Otsuka Pharmaceutical Co., Ltd. Process for producing carbostyril derivative
EP1330249A1 (de) † 2001-09-25 2003-07-30 Otsuka Pharmaceutical Co., Ltd. Aripiprazole wirkstoff mit niedriger hygroskopie und verfahren zu ihrer herstellung

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EG23557A (en) 2006-06-05
HK1073110A1 (en) 2005-09-23
CA2458929A1 (en) 2004-07-09
SI1480953T2 (sl) 2010-12-31
AU2003288755B2 (en) 2005-08-25
JP2012031203A (ja) 2012-02-16
BRPI0305500B1 (pt) 2018-01-23
CN1263742C (zh) 2006-07-12
CA2458929C (en) 2009-09-08
DE60302139D1 (de) 2005-12-08
SI1480953T1 (sl) 2006-04-30
TWI258470B (en) 2006-07-21
MXPA04002519A (es) 2005-04-04
ES2250919T3 (es) 2006-04-16
DK1480953T3 (da) 2005-12-19
EP1480953A1 (de) 2004-12-01
US6995264B2 (en) 2006-02-07
AU2003288755A1 (en) 2004-08-10
DE60302139T3 (de) 2011-02-24
ES2250919T5 (es) 2010-12-03
KR20040093655A (ko) 2004-11-06
WO2004063162A1 (en) 2004-07-29
DK1480953T4 (da) 2010-11-15
ATE308524T1 (de) 2005-11-15
CN1590377A (zh) 2005-03-09
US20040192915A1 (en) 2004-09-30
KR100583667B1 (ko) 2006-05-26
JP5797090B2 (ja) 2015-10-21
DE60302139T2 (de) 2006-07-20
JP2014148511A (ja) 2014-08-21
EP1480953B1 (de) 2005-11-02
AU2003288755C1 (en) 2015-02-19
TW200418840A (en) 2004-10-01
AR042702A1 (es) 2005-06-29
MY129831A (en) 2007-05-31
CA2676216A1 (en) 2004-07-09
BR0305500A (pt) 2004-11-03

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